1. With such a long and varied career behind you as a serial entrepreneur, what motivated you to found Tiger 21? I was trying to solve a problem I had, a problem that it turns out many other people did too.Entrepreneurs are so remarkably focused on making their business successful that they are not typically prepared for what comes next should they actually “make it.” I wanted to create an organization where wealth-builders could come together, learn from one another, and talk about “what comes next.”
  2. If Tiger 21 is so secretive and exclusive, what inspired you to share the insights of their Tiger 21 members with the public through this book? I am not sure any organization that has a web site—and ours is Tiger21.com—can be described as secretive. But we are exclusive. Among other things, to be considered for membership you need to have $10 million in investable assets.But to answer your question directly, I thought it would be helpful for potential members, and everyone else who is trying to create something new, to a) Understand what their journey would probably look like, b) what they could do to avoid some of the pitfalls they would probably encounter along the way, and c) to consider how they could actually make a difference in the world.
  3. What is the most surprising obstacle that entrepreneurs need to overcome that many do not consider when starting out on their own? Ah, you summed up a key takeaway of the book, with one question.  There are 40 obstacles I have identified—that’s why the book has 40 short chapters—starting with a pivotal one: Most people don’t think big enough.  That’s why I called the book Think Bigger.  The other 39 chapters contain straight-forward common sense answers as well.
  4. You work with hundreds of successful entrepreneurs. What have you found to be the most common, valuable traits among them that make them stand out from other business professionals? Grit and determination.  (It is more important that “mere” smarts.) Resilience. And an over-whelming desire to solve a problem—be it a commercial or societal one.
  5. How do the challenges that entrepreneurs face now, differ from those who started out a decade ago? Or even five years ago? The vast majority of the challenges remain constant.  Can you clearly define the problem you are trying to solve? What are the exact steps you need to take to make your vision a reality? How do you find and hire good people?  How will you get funding?  What is the most effective response to the competition?  Those are issues that never change.What has changed is where they competition is coming from—it is remarkably easy for a business to compete globally today, so you may be trying to fend off someone half a world away. That’s possible, in part because of all the technology advances of the last five years, and certainly the last 10—and large corporations are beginning to take strides to become more entrepreneurial as well.
  6. What have you been surprised to learn from the female members of Tiger 21? How have their experiences differed from male members of the group? I sort of knew this, but I really didn’t. I simply didn’t understand how much women are still discriminated against in the workplace. I was horrified by the stories they told about what had—and have—to endure.
  7. Most entrepreneurs start out to solve a problem; not to become wealthy. Once they do become wealthy, why do entrepreneurs have trouble exploring the broader meaning of wealth in their lives? The first problem is most entrepreneurs are not prepared to be wealthy.  They have spent virtually all of their time learning about what will make their businesses successful, and that leaves very little to learn about personal finance.And then there is the question you raised which boils down to, “now that I have it, what should I do with my money.  Since most of the people in the book come from lower to middle-class backgrounds, and tend to live relatively modestly after they have made it—many of them find the thought of flying first class painful, and certainly would never consider flying on a private jet—they need to figure out where money fits in their lives.
  8. Many believe the myth that life becomes easier after an entrepreneur sells their business, and lives off of the proceeds. Why it is in fact harder to manage wealth in today’s environment than it was to create it? I don’t think anyone needs to hold a benefit for successful wealth creators. But you are right they do face specific challenges after a liquidity event such as selling their business. For one thing, they need to determine what comes next.  For another, they need to figure out how they will invest.If you look at something like the Forbes 400 list, which chronicles wealthy individuals, you will see most of them made their money starting companies.  Generating substantial wealth from investments along is rare.
  9. Many entrepreneurs pass their business down to children and other family members. How can family businesses avoid the “shirtsleeves to shirtsleeves” proverb that suggests wealth can’t survive three generations? Communication. Communication. Communication. Does the second generation want to be involved in the business?  How about the third?  If they don’t, but end up working there anyway because of family pressure—or a sense of obligation—things probably won’t go well. If neither the children nor grandchildren wants to be involved, does the family feel a desire to keep the business going as an independent concern, or would a sale be okay. Is the second (and third) generations want to be involved, where should they start? Should it even be in the family business? Might they be better off beginning their careers somewhere else? These are the sort of issues that need to be discuss—early and often.
  10. You dedicate a few chapters of the book to the responsibility of entrepreneurs to use their business and wealth to bettering society. In what surprising ways can wealth be used to leverage philanthropic, political, or family goals and interests? Let me start with a disclaimer. I would never mandate anyone act in a certain way. A wealth-builder can spend his time and money as he sees fit. If he wants to be Scrooge McDuck, to reference a cartoon from when I was a kid, so be it.  (Although I will point out Scrooge McDuck, like Dickens’ Ebenezer Scrooge wasn’t happy.)But I think most of us want to make the world a better place.  Perhaps the biggest surprise is that the skills required to build a successful company—identifying a need and bringing the people and other resources necessary to solve it—are transferable.
  11. The achievements of famous entrepreneurs like Jeff Bezos are mentioned in the news on a daily basis. Who are some relatively new, underdog entrepreneurs that aspiring entrepreneurs can learn from today? You’ve hit on another important point. There is an awful lot we can learn—and emulate—from the entrepreneurs who are the proverbial backbone of our economy, people like those featured in the book.  That why I thought it was important to include them.
  12. What’s the best lesson from your book that an entrepreneur could start applying tomorrow morning to “think bigger”? Start.